BE397338A

BE397338A -

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Publication number: BE397338A
Authority: BE; Belgium
Prior art keywords: parts; dyes; dye; contain; group
Prior art date

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English (en)

French (fr)

Publication of BE397338A publication Critical patent/BE397338A/fr

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239000000975 dye Substances 0.000 claims description 78
150000002148 esters Chemical class 0.000 claims description 25
230000001808 coupling Effects 0.000 claims description 16
238000010168 coupling process Methods 0.000 claims description 16
238000005859 coupling reaction Methods 0.000 claims description 16
150000002170 ethers Chemical class 0.000 claims description 12
238000004043 dyeing Methods 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
150000001298 alcohols Chemical class 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
239000011780 sodium chloride Substances 0.000 claims description 5
230000001034 aminogenic Effects 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 4
239000000543 intermediate Substances 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
150000008049 diazo compounds Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 33
239000002253 acid Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 15
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 14
239000000047 product Substances 0.000 description 12
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
-1 arylamine alcohols Chemical class 0.000 description 11
239000000843 powder Substances 0.000 description 11
239000001632 sodium acetate Substances 0.000 description 11
235000017281 sodium acetate Nutrition 0.000 description 11
238000003756 stirring Methods 0.000 description 11
210000002268 Wool Anatomy 0.000 description 10
239000000203 mixture Substances 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
235000010288 sodium nitrite Nutrition 0.000 description 7
229920000742 Cotton Polymers 0.000 description 6
238000009835 boiling Methods 0.000 description 6
229920002678 cellulose Polymers 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000000875 corresponding Effects 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000007787 solid Substances 0.000 description 6
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 5
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
235000010980 cellulose Nutrition 0.000 description 5
238000006193 diazotization reaction Methods 0.000 description 5
LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000001187 sodium carbonate Substances 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229940095076 benzaldehyde Drugs 0.000 description 4
239000001913 cellulose Substances 0.000 description 4
238000004040 coloring Methods 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
229940093915 Gynecological Organic acids Drugs 0.000 description 3
210000004940 Nucleus Anatomy 0.000 description 3
HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000007792 addition Methods 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000000987 azo dye Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003086 colorant Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000006266 etherification reaction Methods 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N ethylene glycol monomethyl ether Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
238000005755 formation reaction Methods 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
229950000244 sulfanilic acid Drugs 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-Toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
229960000583 Acetic Acid Drugs 0.000 description 2
229920002955 Art silk Polymers 0.000 description 2
241001331845 Equus asinus x caballus Species 0.000 description 2
239000000020 Nitrocellulose Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
240000004713 Pisum sativum Species 0.000 description 2
235000010582 Pisum sativum Nutrition 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic Effects 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000003472 neutralizing Effects 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
229920001220 nitrocellulos Polymers 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
150000004893 oxazines Chemical class 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000008149 soap solution Substances 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000004897 thiazines Chemical class 0.000 description 2
QGSRHLVCBCRYDO-UHFFFAOYSA-N (2,3-diamino-4,5,6-triethylphenyl)-(2-ethylphenyl)methanone Chemical compound CCC1=CC=CC=C1C(=O)C1=C(N)C(N)=C(CC)C(CC)=C1CC QGSRHLVCBCRYDO-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
AGIJRRREJXSQJR-UHFFFAOYSA-N 2H-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
ZRSNZINYAWTAHE-UHFFFAOYSA-N 4-Anisaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
ILWXUPWQRLGQHT-UHFFFAOYSA-N 4-[ethyl(2-methoxyethyl)amino]benzaldehyde Chemical compound COCCN(CC)C1=CC=C(C=O)C=C1 ILWXUPWQRLGQHT-UHFFFAOYSA-N 0.000 description 1
229940040526 Anhydrous Sodium Acetate Drugs 0.000 description 1
RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
229910000906 Bronze Inorganic materials 0.000 description 1
108060002219 DEXI Proteins 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N Diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
241001024304 Mino Species 0.000 description 1
SMQCFBREXKRRGJ-UHFFFAOYSA-N N-(3-hydroxyphenyl)nitramide Chemical compound OC1=CC=CC(N[N+]([O-])=O)=C1 SMQCFBREXKRRGJ-UHFFFAOYSA-N 0.000 description 1
KUDPGZONDFORKU-UHFFFAOYSA-N N-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
241001182492 Nes Species 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
RCTGMCJBQGBLKT-PAMTUDGESA-N Scarlet Red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
KIEOKOFEPABQKJ-UHFFFAOYSA-N Sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 1
241000779819 Syncarpia glomulifera Species 0.000 description 1
VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 description 1
AAAQKTZKLRYKHR-UHFFFAOYSA-N Triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
229940036248 Turpentine Drugs 0.000 description 1
235000005811 Viola adunca Nutrition 0.000 description 1
240000009038 Viola odorata Species 0.000 description 1
235000013487 Viola odorata Nutrition 0.000 description 1
235000002254 Viola papilionacea Nutrition 0.000 description 1
235000012544 Viola sororia Nutrition 0.000 description 1
241001106476 Violaceae Species 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000000240 adjuvant Effects 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000001491 aromatic compounds Chemical group 0.000 description 1
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
239000010974 bronze Substances 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000027326 copulation Effects 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
MRVNLKITQIBNKU-UKOJIYRKSA-L disodium;(4E)-4-(naphthalen-1-ylhydrazinylidene)-3-oxonaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(N\N=C3/C4=CC=C(C=C4C=C(C3=O)S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 MRVNLKITQIBNKU-UKOJIYRKSA-L 0.000 description 1
OPGYRRGJRBEUFK-UHFFFAOYSA-L disodium;diacetate Chemical compound [Na+].[Na+].CC([O-])=O.CC([O-])=O OPGYRRGJRBEUFK-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
150000005002 naphthylamines Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
230000017448 oviposition Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000032696 parturition Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
239000001739 pinus spp. Substances 0.000 description 1
239000001044 red dye Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229960005369 scarlet red Drugs 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
YNBRSWNUNPAQOF-UHFFFAOYSA-M sodium;phenylmethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC1=CC=CC=C1 YNBRSWNUNPAQOF-UHFFFAOYSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000018553 tannin Nutrition 0.000 description 1
229920001864 tannin Polymers 0.000 description 1
239000001648 tannin Substances 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
230000001256 tonic Effects 0.000 description 1
IVNZBWNBYXERPK-DZGBHZPSSA-K trisodium;(8Z)-7-oxo-8-[(4-sulfonatonaphthalen-1-yl)hydrazinylidene]naphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N\N=C3/C(=O)C=CC=4C=C(C=C(C=43)S([O-])(=O)=O)S(=O)(=O)[O-])=CC=C(S([O-])(=O)=O)C2=C1 IVNZBWNBYXERPK-DZGBHZPSSA-K 0.000 description 1
239000002966 varnish Substances 0.000 description 1
230000037303 wrinkles Effects 0.000 description 1